hawai'i with kids recap and recommendations

Aloha! We just returned from Hawai'i, and this time we stayed on the gorgeous island of Kauaʻi. We’ve also been to Maui (before kids) and Oahu, so I’ll share a few of our favorite spots, things to do, and items we brought in this blog post. This trip was not sponsored or paid for in any way, however this post may contain affiliate links. I also saved a bunch of our trip in this IG highlight if you want to check it out!

✈️ Getting there:
San Francisco has multiple direct flights to the islands which makes it really easy. The flight is about 5.5 hours, which isn’t too terrible with kids unless you have a toddler. Leni, my youngest, was 16 months for this trip and I definitely find this to be the hardest age to travel with. My older kids are 4 and 6 and barely spoke the entire time- they watched shows, ate snacks and colored without a peep. Toddlers can be tough on flights because they are so mobile and curious but don’t have a great attention span. Here are a few tips for traveling with little ones around ages 12-24 months:

  • Bring a few “novel” sensory type toys or interactive books but don’t go overboard with packing- they probably won’t hold their attention for long anyway. My kids always go for things like plastic cups and the airline menu.

  • Bring a carrier so you can keep them close while having your other hands free throughout the airport, or to attempt a nap. My favorites are the Artipoppe and Sakura Bloom Scout. If you’re bringing a stroller, you can use it right up to the time you get on the plane and gate check it at no extra cost.

  • To get on the plane, we typically like to board last vs. first. This helps avoid an extra 20-30 minutes of the kids sitting still on the plane. What we sometimes do is have one parent get on with pre-boarding option available to families to set up all the “stuff” like car seats and then the other parent gets on with the baby last.

  • Plan for flights during sleep times, but know that they may not fall asleep exactly at the normal time. For example we booked a flight during Leni’s normal nap time, but she fell asleep much later because there was so much to see and she was excited.

  • Consider buying your toddler their own seat and putting them in their car seat vs. having them as a lap infant. Sometimes if they are contained and in a familiar spot like their car seat they will be more likely to nap, plus you won’t have to wrestle them the whole time. However sometimes this will backfire and they will scream to sit on you anyway, and then it’s money wasted. Having their own seat and being strapped in/ having a seatbelt fastened is still the safest way for them to travel, though.

  • When we arrive we try and get on local time as soon as possible. We do this by strategically offering naps, getting the kids out and running around, and using light/ dark to our advantage. This all depends on which direction you’re going, though, and this blog post has other tips for adjusting to a new time zone and dealing with jet lag.

😴 Setting up for Sleep:

When we first arrive at a destination we like to get the kids sleep spaces set up right away. Here’s how we did things this time:

  • My big kids (ages 4 and 6) shared a queen sized bed in their own room. They’re used to sharing a room at home, so this was pretty seamless! They actually really liked sharing a bed and slept great. Technically, adult mattresses are safe for children over age 2 years, and cosleeping infants with older siblings is not recommended. Check out more on siblings sharing sleep spaces here.

  • We kept the bedtime routine as close to normal as possible! So they had baths/ brushing teeth and getting into jammies, reading books, and lights out with the sound machine while my husband laid with them until they were asleep. We brought our favorite travel sound machine for their bedroom and brought our Sleepout travel curtains just in case there weren’t blackout blinds in the room (code heysleepybaby for 10% off!).

  • Leni bed shared with us in a King sized bed. We made sure to get a room with a King bed and a mattress without a topper that wasn’t memory foam or too soft. Since the bed was a little high and she is over a year old we had her sleep between us like she does at home. However, there have also been times where we’ve felt it was better (and space allowed) for putting the mattress right on the floor. Other tips for bed sharing more safely on vacation:

    • since you can’t necessarily control how low the bed is, if you can’t put the mattress on the ground, I would recommend sleeping in the bed alone with baby if you can so that there’s more space and less risk of them rolling off.

    • If the bed is high, you can add a bumper under the fitted sheet if your baby is over 12 months old. A rolled up towel or pool noodle work great as a little barrier. You can also place couch cushions, pillows etc. on the floor if you’re worried about them falling out of the bed.

    • You don’t want to bed share with the bed against a wall or piece of furniture like a night stand, as this could be a serious entrapment risk.

    • Never sleep with your baby after drinking alcohol, smoking tobacco or taking drugs including medications that cause drowsiness.

    • If your baby is older (6+ months minimum, but 12+ is better) and/or you can get a King sized bed, your baby might be safest between you and your partner as long as there is no dip in the bed and the mattress is firm. These issues could create an unsafe situation for rebreathing especially with young babies.

    • Always be sure to follow the Safe Sleep Seven, especially on vacation. The safest option for babies that don’t normally bed share (or if the sleep space isn’t ideal) is to have a separate space like a pack’n’play for baby, but keep it right next to your side of the bed so they still feel close to you. Above all, use your best judgement and follow the guidelines to the best of your ability. For more on safe sleep options while traveling, check out this post as well as my free travel guide!

Kauaʻi Recommendations

Where we stayed:

We stayed at the Waipouli Beach Resort which is located right on the beach between Kapaa and Wailua on the east coast of Kauai. Waipouli Beach Resort is less than 10 miles from Lihue Airport which made it super convenient. Although it feels like an island paradise once you’re inside the resort, the modern conveniences mere steps away are hard to beat. Right across the street there’s a Safeway grocery store, a Starbucks, a McDonalds, Shave Ice, Sushi, and ABC Store. It’s also super close to the popular Coconut Marketplace which has a bunch of other food and shopping options. About a mile away is the little downtown area of Kapaʻa with lots of great local shops if you’re looking for gifts or souvenirs, other cute cafe’s, juice and smoothie shops, restaurants etc.

This location was great because we were kind of in the middle of the coast. We could easily drive to the southern tip or the northern tip of the island in less than 40 minutes, which made day trips really doable with the kids.

The hotel had condo-style rooms. We stayed in H105, which is on the ground floor with an ocean view, kitchen, and 2 bedrooms as well as 2 huge bathrooms. It was very close to the pool as well as the beach. Being on the ground level was amazing because the kids could run right outside and play in the huge grassy lawn, and we had a table and chairs for eating outside as well. The pool at this resort was incredible for kids. There was a big pool with winding “rivers” and waterfalls, plus two water slides. The pool was a little chilly (we went in March) but there were also several hot tubs including a “family” hot tub where kids were welcome. There is also a separate kids pool right in the same area, which I appreciate, that offers a pebble bottom and wading area perfect for toddlers. You can also rent things like floaties, noodles, and life jackets right on site.

The only downside to this resort for us was that there wasn’t really a breakfast or lunch option on the premises, and no pool bar/ restaurant. There is the restaurant on property called Oasis on the Beach, right behind the pool area, which looked good for grown-up dinners but we didn’t try it. For food during the day we typically ate in our condo (went grocery shopping our first day) or checked out a local restaurant. We would have loved a resort that allowed for poolside lunches or a cocktail during the day. Otherwise we were super impressed and happy at this place!

What we ate:

We love staying in condo’s and Air bnb’s with kids because it allows for more space but also allows you to cook your own meals. This helps cut costs significantly when traveling with kids. We got groceries and kept things like eggs, bread, fruit and veggies plus snacks and sandwich stuff stocked in our condo so most breakfasts and lunches were just like they are at home. This also helps with toddlers who are selective about what they eat and like familiar foods to be available. That being said, Marley and I LOVE food and it’s one of our favorite things about going to new places. We love to try the local cuisines. One tip is to use Tiktok as your google. I know it sounds weird, but we searched Kauai in Tiktok and found SO many amazing videos and got a lot of our recommendations from there vs. using something like Google, Yelp or Trip Advisor.

Near our resort was one of our favorite places for breakfast, Collab Cafe - they had incredible coffee, fresh juices, delicious breakfast sandwiches, toasts and pastries. We also appreciated the selection of kids books and toys to keep the little ones busy while we waited for our food. It was a bit pricey so we definitely didn’t do this every day, but it was great for when we were running low on breakfast options or just needed to get out in the morning.

We also heard great things about Java Kai for coffee and breakfast (the Macadmia Nut Latte!) but didn’t make it there this time. Lots of our family members went more than once! We checked out the coffee and smoothies from Positive Coffee and got delicious Malasadas (made fresh on Tues, Thurs, and Sat) from Passion Bakery.

For lunch and dinners we loved Pono Market and Fish Bar Deli, and we also got takeout from Sleeping Giant Grill and Chicken in a Barrel several times!

All of these restaurants were a short drive or less than 10 minute walk.

While out and about, we tried some other island specialties. When we visited Popui Beach we stopped for lunch right across the street from a playground at Puka Dog for Hawaiian Style Hot Dogs, which were delicious! On the way home from the beach we stopped by Konohiki Seafood and got some delish poke plus fried shrimp, chicken and sushi. Up north in Princeville, before visiting Anini Beach, we went to Foodland grocery store for Poke and Pie. We also got to try the amazing desserts from Kilauea Bakery & Pizza. Near Hanalei Beach, we had Poke (Marley says the best he’s ever had!) from Hanalei Dolphin Fish Market then took the kids to get AMAZING shave ices and ice cream at Wishing Well. Our last meal on the island was incredible, at a hole-in-the-wall type place in Lihue right by the airport called Hamura Saimin which had delicious Japanese-Hawaiian food. We loved the noodles, soup, fried dumplings and chicken skewers. You sit at the counter and it’s SUPER fast so perfect for a pre-flight meal.

What we did:

Aside from hanging by the pool and at our resort’s beach, we did get to explore a bit of the island. While there are tons of things to do and see on Kauaʻi we mainly stuck to beach activities since that’s what our kids love doing most! We visited these beaches:

Anini: Gorgeous beach that’s not too crowded, with lots of shallow water. We drove all the way to the end, which was a bit of a bumpy ride but super worth it! This beach is on the northern part of the island which from what we understood gets quite cloudy and rainy in the afternoons, so go in the morning! There’s lots of trees here so natural shade is easy to find. The water here was pretty calm and good for things like paddleboarding, swimming and snorkeling.

Hanalei: Incredible mountain views, but definitely rougher waves. Lots of people were surfing and boogey boarding here, which was cool to watch! This beach was pretty exposed without much natural shade on the beach, so bring a tent or umbrella. There are pavillions, picnic tables, bathrooms and foot showers here. There are technically 3 sections to this beach depending on what you want to do, the ages of your kids etc.

Popui: This was where we saw the sea turtles right on the beach! Definitely a populated beach, but fun to check out for a couple of hours. There’s also a grassy area and playground connected to this beach as well as picnic tables, restrooms and lifeguards.


Lydgate: We went here a few times since it was so close to where we stayed and definitely the most kid-friendly. This is a huge state park and there’s an absolutely incredible playground as well as bathrooms, picnic tables and showers. The kids loved this beach best because there are two large rock-protected lagoons which were very shallow, warm and calm. We also saw tons of fish at this beach so it’s great for snorkeling!

Marley also went on a Kayaking and Hiking trip for a half day with his cousins, and loved it.


What we packed:

My favorite new packing hack using this over-the-door organizer was seriously SUCH a space and time saver! Having the kids outfits all on display made it so easy to grab and go, plus made it clear when we were running low and needed to do some laundry (which we had in our condo!). I packed by kid and by outfit. So I’d do a row for each kid, and each pocket had a FULL outfit (undies, shorts, top or dress) all rolled up. Swim stuff and PJ’s went in the last row and at the bottom.

For packing to come home, rather than packing up outfits I packed items by type (Otto’s shorts all together, t shirts all together, etc.) so when we came home I could just grab the stuff to throw back into their drawers. This made packing SO easy and I can’t recommend this method enough! The organizer rolled up and fit into a standard sized suitcase which we checked. I also always keep one extra “just in case” outfit in a carry-on along with other essentials just in case bags get lost.

For 8 days, we packed 5 outfits per kid, plus 3 pairs of PJs and 3 swimsuits plus their sunhats (big kids here and Leni’s here and here). I would have packed slightly more if we weren’t going to have laundry on site. One thing I didn’t bring that I wished we’d had was a sweatshirt/ light jacket for each of us- it got chilly at night in March.

We didn’t need to pack tons of diapers or snacks because we knew the grocery store was right there. We also didn’t pack a lot of toys or other activities because we rented from BabyQuip! This is one of my favorite travel hacks ever. You can rent nearly anything for just a few bucks per day, and it’s usually supporting a local mom/ family! We rented a double stroller, beach tent, sound machine, high chair, baby hiking backpack, sand toys, and a big bin of assorted toys (I just entered kids ages and they gave us a perfect assortment of stuff they LOVED!). You can also rent things like car seats, cribs, monitors, baby bath tubs and more. It’s SO easy and convenient. You can use code SLEEPY20 to get $20 off your order of $100 or more! Babyquip serves families in hundreds of cities across the US, Canada, Mexico, Caribbean, Australia and New Zealand.

In the kids carry-ons we packed them each a water bottle, bag of snacks, ipad and headphones (not really necessary since our flight had screens, but not all do anymore!) and some coloring/ markers. That’s it!

We also brought along our travel car seats, which we check. For Leni (16 months) we used this Cosco seat which is great and super lightweight. When she was littler we used the Doona for travel and it was super convenient! For Noe, we have the WAYB Pico seat, which is honestly incredible. It folds up and is SO compact and easy to carry around. Since Otto is big enough now we just use a booster for him, the same one we have at home which is a Clek Booster (back is removable!). At the airport we usually stick all the seats in a carseat bag (all 3 of these fit in one bag!) and check it at no charge. For more on car seats and travel check out this episode of NOTU I did with expert Jamie Grayson.


What I wore:

I tried to link up the most-asked about items from our trip on my LTK store, which I try and update regularly for you! Here were the swimsuits, coverups, outfits, hats, sandals etc. I brought:

Roll-up Visor Sunhat and Bucket Hat | Sunglasses: Oval Shape and Retro Cat Eye

Coverups: Crochet dress and White button down (so versatile I wear it as a top, too!) | Shoes: Flip Flops and Birkenstocks

Jewelry: similar Pearl Necklace and Colorful Beaded Choker| Denim Shorts from Target (dupe for $$$ Agolde ones!)

White Swimsuit | Green Swimsuit | Red Swimsuit (all nursing friendly with good booty coverage!)

Oahu Recommendations:

As I said at the beginning of this post, this was our very first trip to Kauaʻi and we can’t wait to go back someday to see all the other things this amazing island has to offer. We’ve also visited Oahu with our kids twice, staying in both Honolulu and Haleiwa (North Shore). Here are some of the things we loved there:

Honolulu/ Waikiki:

Walking along Waikiki Beach and going to Barefoot Beach Cafe

Waikiki Aquarium

Leonard’s Bakery for Malasadas

Diamondhead General Store

Diamondhead Market and Grill

Haleiwa:

Big Wave Shrimp Truck

Farm to Barn Cafe

The Beat Box Cafe

Kaimana Shave Ice

We also did our maternity shoot here when I was pregnant with Leni. We worked with Sophia from The Sophia Co and she captured some truly amazing shots that are like ART! If you’re going to be on Oahu she is incredible for family photos!

Other Places we Went:
Hanauma Bay Nature Preserve

Kapolei Beaches

Waimānalo Beach

We always have such a great time in this incredible place, even though traveling with kids can be completely exhausting and soul-crushing. It’s in a fun way, ya know!? For more on traveling with kids and alllllll the tips check out my giant Travel with Babies and Toddlers post here.

Listen to me talk more about how to get into the spirit of traveling with kids, reducing stress etc. in this episode of NOTU 🎧

Dont’ forget to grab this FREE guide, which goes into all the logistical details of traveling while pumping or breastfeeding, cosleeping safely on vacation, packing tips and so much more! ⬇️



Rachael Shepard-Ohta

Rachael is the founder of HSB, a Certified Sleep Specialist, Circle of Security Parenting Facilitator, Breastfeeding Educator, and, most importantly, mother of 3! She lives in San Francisco, CA with her family.

https://heysleepybaby.com
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